Keewaydin Island vacation rentals

We found 10,488 vacation rentals — enter your dates for availability

Welcome to the enchanting Keewaydin Island, where pristine beaches meet crystal-clear waters, inviting you to unwind in a sun-soaked paradise. Stroll through charming streets that echo local culture, and indulge in family-friendly activities that cater to all ages. Choose from cozy condos and private homes, each designed for comfort and convenience, ensuring your group enjoys the perfect blend of relaxation and adventure. Embrace the home-like experience of a vacation rental, offering the space and amenities you need for a memorable getaway.

Holiday rentals with weekly discounts - Keewaydin Island

Showing deals for:Jan 1 - Jan 8

Living area
Exterior
Pool
Outdoor dining
Exceptional
(54 reviews)

Steps from Bonita Beach! Great family home with a pool on salt water canal!

Bonita Springs

9% off
$1,024
$7,171 for 7 nights
All fees included
Steps from Bonita Beach! Great family home with a pool on salt water canal!
Relax in this stylish bedroom with comfy bedding & natural light
Relax, stream a movie, or catch the game—this is your comfy vacation hub
Cozy daybed perfect for reading, napping, or an extra guest’s retreat
Curl up with coffee and a book in this sun-drenched, peaceful sitting area
Exceptional
(15 reviews)

Beach Escape for Families + Friends • 2 Min to Sand

Bonita Springs

9% off
$756
$5,291 for 7 nights
All fees included
Beach Escape for Families + Friends • 2 Min to Sand
Room
Living area
Terrace/patio
Private kitchen
Exceptional
(18 reviews)

🐾 Dog Friendly, Spacious Beach Retreat, only Steps to Sugary Sand, Conveniences and all the Fun!

Fort Myers Beach

8% off
$236
$1,652 for 7 nights
All fees included
🐾 Dog Friendly, Spacious Beach Retreat, only Steps to Sugary Sand, Conveniences and all the Fun!
Dining
Walk or bike to the white sandy beach!
Living area
Private kitchen
Exceptional
(33 reviews)

COZY BEACH HOME! Walk/Bike to Beach, Dining, Shops, Near Ritz-fenced doggie area

Naples

9% off
$316
$2,212 for 7 nights
All fees included
COZY BEACH HOME! Walk/Bike to Beach, Dining, Shops, Near Ritz-fenced doggie area
Terrace/patio
Private kitchen
Living area
Dining
Exceptional
(10 reviews)

Luxurious Modern 4BR, Heated Pool near Beach and Mercato! Newly Renovated!

Naples

9% off
$589
$4,120 for 7 nights
All fees included
Luxurious Modern 4BR, Heated Pool near Beach and Mercato! Newly Renovated!
The outside space features plenty of sitting areas, including a hammock.
Enjoy a quiet evening in this living room with plenty of seating.
Enjoy a quiet evening in this living room with plenty of seating.
You can have dinner at this modern dining table with seating for 6.
Exceptional
(17 reviews)

4BR | Heated Pool | Hot Tub | Lanai | Gazebo | PS 4. Beautifully remodeled. Walk to dining & Publix, just 5 mins to the beach. We provide premium beach gear and a fully stocked chef's kitchen. Your perfect family getaway!

Marco Island

7% off
$678
$4,747 for 7 nights
All fees included
4BR | Heated Pool | Hot Tub | Lanai | Gazebo | PS 4. Beautifully remodeled. Walk to dining & Publix, just 5 mins to the beach. We provide premium beach gear and a fully stocked chef's kitchen. Your perfect family getaway!
Game Room / 89" Air Hockey / Checkers / Chess / 4 In A Row / 65" Smart TV
Very close to the beach
Game Room / 89" Air Hockey / Checkers / Chess / 4 In A Row / 65" Smart TV
Game Room / 89" Air Hockey / Checkers / Chess / 4 In A Row / 65" Smart TV
Exceptional
(111 reviews)

THE WAVES HOUSE! 7 minute walk to the beach, 2 minute walk to the JW Marriott

Marco Island

5% off
$1,468
$10,277 for 7 nights
All fees included
THE WAVES HOUSE! 7 minute walk to the beach, 2 minute walk to the JW Marriott
Property grounds
Pool
Private kitchen
Living area
Exceptional
(19 reviews)

Waterfront Beach Rental with Boat Lift!

Marco Island

5% off
$1,155
$8,087 for 7 nights
All fees included
Waterfront Beach Rental with Boat Lift!
Room
Exterior
Living area
Interior
Very Good
(10 reviews)

Walk To Beach, North End Restaurants, Night Life Steps Away!

Fort Myers Beach

8% off
$266
$1,859 for 7 nights
All fees included
Walk To Beach, North End Restaurants, Night Life Steps Away!
Interior
Private kitchen
Living area
Dining
Excellent
(37 reviews)

5 O'Clock Somewhere getaway-Walk/Bike to Beach,Shops ,Fenced private doggie area

Naples

9% off
$306
$2,140 for 7 nights
All fees included
5 O'Clock Somewhere getaway-Walk/Bike to Beach,Shops ,Fenced private doggie area
Living area
Dining
Exterior
Living area
Excellent
(36 reviews)

BEACHSIDE COZY GETAWAY! Walk/Bike to Beach,Dining,Bars,Small fenced yard for pet

Naples

9% off
$312
$2,184 for 7 nights
All fees included
BEACHSIDE COZY GETAWAY! Walk/Bike to Beach,Dining,Bars,Small fenced yard for pet
Interior
Heated Pool with jacuzzi
Dining Room (6)
Guest room #2 Queen Bed
Exceptional
(18 reviews)

Desired Southern Exp Waterfront SW Quadrant Pool Home! Walk to Crescent Beach!

Marco Island

9% off
$890
$6,231 for 7 nights
All fees included
Desired Southern Exp Waterfront SW Quadrant Pool Home! Walk to Crescent Beach!
Private kitchen
Property grounds
Pool
Room
Exceptional
(61 reviews)

Estero Beach & Tennis Club, 404C, Pet Friendly- Beach Front- Internet

Fort Myers Beach

9% off
$320
$2,237 for 7 nights
All fees included
Estero Beach & Tennis Club, 404C, Pet Friendly- Beach Front- Internet
Living area
Interior
Dining
Interior
Exceptional
(38 reviews)

Marco Island House Walk Distance to Beaches

Marco Island

9% off
$519
$3,635 for 7 nights
All fees included
Marco Island House Walk Distance to Beaches
Outdoor dining
Living area
Pool
Private kitchen
Exceptional
(14 reviews)

Blue Anchor Villa luxury 4 bedroom Home

Marco Island

5% off
$1,152
$8,063 for 7 nights
All fees included
Blue Anchor Villa luxury 4 bedroom Home
Interior
Exterior
upstairs living room
lower level entrance, beach and gear storage
Exceptional
(65 reviews)

Vanderbilt Beach House, Perfect for 2 families, Pet friendly, Bikes beach gear

Naples

9% off
$650
$4,550 for 7 nights
All fees included
Vanderbilt Beach House, Perfect for 2 families, Pet friendly, Bikes beach gear
Property grounds
Beach
Exterior
Living area
Wonderful
(27 reviews)

BEACH TIME! WALK/BIKE TO THE BEACH-Min to shops, dining, movies-Fenced backyard

Naples

9% off
$323
$2,263 for 7 nights
All fees included
BEACH TIME! WALK/BIKE TO THE BEACH-Min to shops, dining, movies-Fenced backyard
Dining
Large and bright entertainment area
Private kitchen
Chefs kitchen
Exceptional
(40 reviews)

New, modern pool villa in Naples Park / 15 min. walk to the beach

Naples

18% off
$545
$3,812 for 7 nights
All fees included
New, modern pool villa in Naples Park / 15 min. walk to the beach
Property grounds
Living area
Dining
Pool
Exceptional
(10 reviews)

Naples Beach condo. First floor easy access- Walk to Vanderbilt Beach

Naples

8% off
$362
$2,531 for 7 nights
All fees included
Naples Beach condo. First floor easy access- Walk to Vanderbilt Beach
Pool
Exterior
Property grounds
Room
Exceptional
(20 reviews)

Luxury apartment by the beach - Marco Beach Ocean Resort

Marco Island

9% off
$428
$2,998 for 7 nights
All fees included
Luxury apartment by the beach - Marco Beach Ocean Resort
Interior
Exterior detail
Pool
Exterior
Exceptional
(98 reviews)

Marco Beach Ocean Resort - 5th Floor Private Garden terrace Room Sleeps 4!

Marco Island

8% off
$932
$6,521 for 7 nights
All fees included
Marco Beach Ocean Resort - 5th Floor Private Garden terrace Room Sleeps 4!
Bathroom
Living area
Exterior
Room
Exceptional
(27 reviews)

Private Suite near the Beach

Naples

9% off
$135
$942 for 7 nights
All fees included
Private Suite near the Beach
Backyard Waterview
Back Patio
Front
Kitchen
Excellent
(9 reviews)

Private 1st floor of house with pool, dock, 3 blocks to beach and pet friendly

Marco Island

18% off
$719
$5,036 for 7 nights
All fees included
Private 1st floor of house with pool, dock, 3 blocks to beach and pet friendly
Exterior
Pool
Interior
Property grounds
Exceptional
(156 reviews)

Perhaps the Best View in the Building - Developer's Personal Unit at one Time!

Fort Myers Beach

9% off
$276
$1,933 for 7 nights
All fees included
Perhaps the Best View in the Building - Developer's Personal Unit at one Time!

Find the best place to stay - Keewaydin Island

Saturday Farmers Market during season
Two blocks away
Premier Host
10
Exceptional
143 reviews
Romance on 3rd St South Old Naples
3 pools!
Premier Host
9.8
Exceptional
137 reviews
3 Pools, lazy river, walk to 5th ave restaurants!
Beach
Premier Host
10
Exceptional
44 reviews
Olde Naples beautiful Condo Steps to Pier, Beach, Sunsets and restaurants!
300 STEPS TO THE NAPLES PIER
Premier Host
9.8
Exceptional
209 reviews
1st floor by pool, beach and 3rd St. S coffee shops, restaurants and farmer Mkt
Terrace/patio
Premier Host
10
Exceptional
16 reviews
Cypress Cove
Sun N Fun Lagoon park in Collier County
Premier Host
10
Exceptional
35 reviews
FALL SAVINGS! New pool - 2 miles to Beach-5th Ave, 2 King Beds, Bikes
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Find out more about Keewaydin Island

Why visit Keewaydin Island

  • Stunning Beaches: Enjoy the pristine sandy shores, perfect for sunbathing and beach activities.
  • Outdoor Adventures: Engage in fun activities like boat rentals and excursions to explore the beautiful waters.
  • Family-Friendly Atmosphere: The island caters to families, providing various options for outdoor fun and relaxation.
  • Charming Local Community: Experience the friendly vibe of nearby Naples, enhancing your vacation experience.
  • Diverse Accommodations: Choose from waterfront properties to cozy retreats, ensuring a memorable stay.

Popular types of accommodation around Keewaydin Island

Your adventure to Keewaydin Island awaits, and selecting the perfect place to stay is the first step. Explore an array of popular vacation rentals, including condos, private homes, and convenient apartments. Whether you're after waterfront properties or a cozy retreat with amenities galore, you'll find the ideal accommodation to make your getaway unforgettable. Dive into the options and secure your dream rental today.

  • Condos: The top choice for visitors to Keewaydin Island, offering modern amenities and stunning views, perfect for a relaxing getaway.
  • Houses: A great option for families and groups, these homes provide spacious living and a home-like atmosphere.
  • Apartments: A convenient choice for solo travelers or couples, featuring essential comforts in a compact space.
  • Villas: Luxurious and spacious, these properties provide a high-end vacation experience with beautiful surroundings.
  • Cottages: Quaint and cozy, ideal for a peaceful retreat near the beach or in nature.**

Top attractions near Keewaydin Island

Keewaydin Island is an ideal destination for beach lovers and families seeking outdoor adventures. Visitors can explore beautiful beaches, vibrant streets, and marinas, with activities catering to those looking for cultural experiences. Popular attractions include boat rentals and trips to Keewaydin Island, ensuring a memorable vacation filled with fun and relaxation in this picturesque setting.

  • Naples Beach: Experience the soft, white sands and stunning sunsets at Naples Beach, just 4 miles from Keewaydin Island. Enjoy beach vibes with opportunities for sunbathing, swimming, and building sandcastles, making it a perfect spot for relaxation and family fun.
  • Fifth Avenue South: A vibrant street located 5 miles away, Fifth Avenue South offers city vibes with upscale shops, art galleries, and gourmet restaurants. Stroll through this bustling area to soak in the local culture and enjoy a delightful dining experience.
  • Naples Pier: Just 4 miles from Keewaydin Island, Naples Pier features excursion vibes with fishing, dolphin watching, and scenic walks over the water. This iconic destination is perfect for enjoying beautiful ocean views and capturing memorable photographs.

Things to do recommended for couples

Looking for a romantic getaway on Keewaydin Island? Enjoy a fun round of mini-golf at Coral Cay Adventure Golf, only 5 miles away, or indulge in thrilling water sports at Marco Island Ski & Watersports, located 10 miles from the island. Perfect for couples seeking adventure.

Things to do recommended for families

Your family will have a great time at East Naples Community Park, only 3 miles away, enjoying wellness activities. For some adventure, head to Sun N Fun Lagoon, 14 miles from Keewaydin Island, a lively waterpark perfect for all ages. Eagle Lakes Community Park, 4 miles away, offers more relaxation.

Things to do recommended for groups

Groups visiting Keewaydin Island can enjoy shopping at Tin City, just 5 miles away, and experience its lively atmosphere. For outdoor enthusiasts, TPC Treviso Bay and Evergreen Golf and Country Club, both 3 to 5 miles away, offer excellent golfing opportunities in a beautiful setting.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Keewaydin Island

If you're traveling with a group, family, pets, or planning an extended stay, be sure to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Keewaydin Island with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Keewaydin Island with young kids: Traveling with little ones can be quite a challenge. It's important to prioritize their comfort and safety, along with amenities that are suitable for their age, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Keewaydin Island: For many families, a vacation wouldn’t feel complete without their furry companion. If this resonates with you, consider exploring Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Keewaydin Island: If you're in search of vacation rentals that offer discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to consider adding amenities like a parking space, a well-equipped kitchen, or a private pool to your search criteria.

Where to stay near Keewaydin Island

Keewaydin Island, Florida, offers a perfect blend of sandy beaches and outdoor adventures for families and couples alike. Explore the tranquil barrier island atmosphere, indulge in romantic strolls along the shore, or enjoy excursions with friendly locals. Nearby Naples enhances your experience with its vibrant community and family-friendly vibe. Whether you're seeking relaxation or adventure, Keewaydin Island is an ideal destination for your next getaway.

  • Naples: Nestled along the Gulf of Mexico, Naples is a vibrant city known for its beautiful beaches and upscale atmosphere. Keewaydin Island, located within its jurisdiction, is a serene getaway that complements the city's lively coastal charm. Visitors flock to Naples for its luxurious resorts, stunning shopping centers, and world-class golf courses. The pristine sandy beaches and family-friendly coastal parks provide a perfect backdrop for outdoor activities. Must-visit attractions include the picturesque Naples Pier and the local theme parks, which cater to both adventure seekers and families looking for fun.
  • West Naples: Just three miles from Keewaydin Island, West Naples is a charming neighborhood that offers a delightful blend of leisure and recreation. Known for its welcoming atmosphere, visitors can indulge in a variety of outdoor activities and enjoy the local beaches, perfect for families looking to unwind. The area boasts excellent shopping options, from local boutiques to larger mall centers. Golf enthusiasts will also find plenty of options to tee off. Highlights include family-friendly beaches and nearby islands that provide further opportunities for exploration and relaxation.
  • Port Royal: Port Royal is another picturesque neighborhood located approximately three miles from Keewaydin Island. This upscale enclave is famed for its stunning waterfront properties and serene environment, ideal for families and outdoor enthusiasts. Visitors can enjoy local shopping areas and top-notch golf courses while soaking in the area's natural beauty. The nearby beaches and islands make it a perfect spot for sun and sand lovers. Port Royal's exclusive atmosphere, combined with its proximity to Naples and outdoor adventures, makes it a must-visit destination during your stay.

Best time to go to Keewaydin Island

If you're planning a trip to Keewaydin Island, Naples, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in March to April and June, while off-peak times, like August and October to November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January65.7°F (18.7°C)No Rain (Dry)Mostly SunnyAverageAverage
February68.2°F (20.1°C)No Rain (Dry)SunnyAverageSlightly High
March70.3°F (21.3°C)No Rain (Dry)SunnySlightly HighSlightly High
April75.4°F (24.1°C)No Rain (Dry)SunnySlightly HighAverage
May78.8°F (26.0°C)Light RainMostly SunnyAverageAverage
June82.2°F (27.9°C)Light RainMostly SunnySlightly HighAverage
July83.7°F (28.7°C)Light RainMostly SunnyAverageAverage
August84.0°F (28.9°C)Light RainMostly SunnySlightly LowSlightly Low
September82.4°F (28.0°C)Light RainMostly SunnyAverageSlightly Low
October78.6°F (25.9°C)Light RainMostly SunnySlightly LowSlightly Low
November73.0°F (22.8°C)No Rain (Dry)Mostly SunnySlightly LowAverage
December69.3°F (20.7°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Are you hoping to save money on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, booking a longer stay can lead to considerable savings. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway at a great value.

Vrbo Trips: Effortless planning

Vrbo's user-friendly Trip Board offers you a convenient way to plan your travel. You can start new trips, pick up right where you left off, or easily view and organize your travel plans. All the properties you’ve saved or booked are neatly categorized into Potential, Upcoming, or Current Trips for your convenience. To explore Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Travel to charming Keewaydin Island

The beaches and surrounding scenery provide a peaceful ambiance to your vacation home in Keewaydin Island. This romantic city allures visitors with its restaurants and shopping. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in and around Keewaydin Island

Do you want to find attractions to visit in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Keewaydin Island a fun place to get away. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • TPC Treviso Bay (3.2 mi / 5.1 km)
  • Flamingo Island Course - Lely Resort (5.1 mi / 8.2 km)
  • Naples Zoo at Caribbean Gardens (6.8 mi / 11 km)
  • Tiburon Golf Club (12.3 mi / 19.7 km)
  • La Playa Golf Club (14.5 mi / 23.4 km)
  • Naples Grande Golf Club (7.4 mi / 11.9 km)

Exploring the natural features in Keewaydin Island

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Keewaydin Island is a great spot to appreciate mother nature. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Naples Botanical Garden (2.7 mi / 4.3 km)
  • East Naples Community Park (2.8 mi / 4.5 km)
  • Naples Bay (4 mi / 6.4 km)
  • Naples Beach (4.4 mi / 7.1 km)
  • Lowdermilk Beach Park (6.6 mi / 10.6 km)
  • South Naples and Marco Island Beaches (7.2 mi / 11.6 km)

Frequently asked questions

How much does it cost to rent a vacation rental in Keewaydin Island?
Property type, season and length of stay are some of the things that can determine the price of a vacation home. Simply click on your travel dates to find your perfect fit. From cozy country cottages to plush villas, all Vrbo vacation rentals offer incredible value.
How much does it cost to rent a beach house in Keewaydin Island?
When you travel and the size and style of the property will influence the cost of your beachside escape. Put in your Keewaydin Island travel dates to see your options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use the filters to select the amenities and features you want in your beach house.
How old do you have to be to rent a vacation rental in Keewaydin Island?
The minimum required age is normally 16, 18 or 21. It can differ from one property to another on Vrbo, so check the rules of your preferred Keewaydin Island vacation rental before you book.
How long can I rent a vacation rental in Keewaydin Island for?
How long you can book a vacation rental in Keewaydin Island is up to the property. Just enter your preferred dates to display a list of options offering extended stays. With many features such as air conditioning and kitchens, as well as some offering discounted weekly or monthly prices, you're sure to get somewhere perfect to call your home away from home in Keewaydin Island.
Does Vrbo offer discounts for vacation homes in Keewaydin Island?
On Vrbo, we've got plenty of fabulous bargains and discounts for Keewaydin Island. Check out our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you're looking for a weekend retreat or a longer stay, Vrbo has lots of options for all styles and budgets.

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